In this episode, we
delve into lifelong learning – the key to growing your superpowers,
whether you’re interested in taking the next step in your career or
feeding your side hustle. We gathered expert tips and advice on how
to keep learning and how to decide what new skills will most
benefit you. We also get the scoop on how to get the most out of
learning conferences and what it takes to earn a certification from
Microsoft.

Listen to this episode
for a chance to win a free three-month subscription to LinkedIn
Learning! One lucky Windows Insider will be selected to access the
entire LinkedIn Learning library of 10,000 courses. To enter, tweet
about the new talents and knowledge you’ve gained through LinkedIn
Learning, and we’ll randomly select one entrant to win. So, let us
know on Twitter how you’ve used LinkedIn Learning to up your game.
Then, tag your Tweet with #alwaysbelearning and #windowsinsider to
be entered into the drawing. Entries must be received by Wednesday,
April 18.

Today, we're talking lifelong learning, that is, how to continue
growing your superpowers, whether you're interested in taking the
next step in your career, feeding your side hustle, or an amazing
new hobby.

Our first guest is "the" ultimate lifelong learner. She
took a break from her busy job at LinkedIn to share pro tips for
acquiring at least three new skills every year.

SAVANNAH BARRY: I'm Savannah Barry, and I
am a marketing manager at LinkedIn, and I work primarily on
LinkedIn Learning.

JASON HOWARD: Awesome. Welcome to
the studio.

SAVANNAH BARRY: Thank you. Thank
you for having me.

JASON HOWARD: So, we've heard from our
colleagues at LinkedIn that you are "the" ultimate lifelong learner
and are really savvy in terms of being able to work on new skills
to grow your career. Would you mind sharing with everybody
your method for doing this?

SAVANNAH BARRY: Yeah, totally. So,
I'm just a curious person in general. If there is a problem
that I come across, I'm very eager to learn how to fix it. I
have a hard time, like, just kind of stepping back and saying,
"Like, okay, like, someone else handle this problem." Which I
think has driven me to be naturally a very curious learner, and
kind of have a desire to learn a lot.

So when I first joined, I actually joined the Lynda.com team
prior to LinkedIn acquiring Lynda.com, and I worked on our
enterprise marketing team there. And a great example about
what I did there was we needed some e-mails to be coded, and we had
to basically rely on an engineering team to build them. And I
was, like, "This is not efficient, I cannot get stuff done in the
timely manner that I would like it to be."

So I basically taught myself how to code e-mails, which I had no
idea how to do. But I had a need. I had a problem I
needed to overcome, I had some campaigns I wanted to ship, and
yeah, I spent months after work learning HTML, taking courses on
Lynda, LinkedIn Learning, reading books -- just like basically
picking my fiancée's brain, like, "Please teach me how to do
this." And at the end of the day, you know, I think it, in
general, has made me a better marketer. That's a great
example of just like one very tactical thing I did.

But I reserve an hour out of my week, every single week, to
learn. Truly, I have a calendar invite on Friday, it actually
will be after this podcast, where I will basically just reserve at
least an hour just to sit down and read something that's like
relatable to my career, watch an online course, listen to a podcast
-- really, anything that can kind of help me achieve my goals,
which I think that has been on my calendar as long as I can
remember, so that's kind of how I can carve out time.

JASON HOWARD: Well, it sounds like you
have a bit of a system -- almost like you've planned out time to go
and learn new things. Can you describe some of the, like, the
mindset and the process you have behind that?

SAVANNAH BARRY: Yeah. I think just
knowing that you need to make the time, like, kind of just clearing
things out of your brain, off of your desk.

I actually go to like a different place. I'll go to a
coffee shop, I'll go to a different room in my house, just kind of
find a place where I feel a little bit inspired, just to really sit
down and focus on the task at hand.

So, for example, right now, I'm learning UX design. So I
got a bunch of books. And this all stemmed because I was
using an app and I was, like, getting really frustrated at
it. And I was, like, "Why am I getting so frustrated at this
app?" And there's such a psychology behind how we, like,
interact with things. And I was very keen to
understand.

So that is currently what I'm doing. And I have a book in
my car that I will be diving into when I get done here, and
probably go into a coffee shop or something and read.

JASON HOWARD: So one of the things that I
was kind of told on the side is that you have a vision board,
right? And you list personal and professional skills --

SAVANNAH BARRY: Yes.

JASON HOWARD: -- that you want to
learn. What prompted that? Where did that come
from? I don't have a whiteboard at home, so -- I mean, you
know, you might inspire me to go out to Staples or something and go
get a whiteboard this afternoon.

SAVANNAH BARRY: Yes. I personally
think that everyone needs vision boards. I try to make my
family and friends make vision boards with me. It hasn't
really caught on with them as much as it's caught on with me.
(Laughter.)

But this year, I actually did it on a whiteboard, and I like
drew out what I wanted to do.

So I draw, like, pictures and goals and just what I want my year
to look like. And that always consists of three professional
and three personal things I want to learn.

So where did it start? I think I was like in college and
one of my psychology classes, like, talking about vision boards or
something -- I don't know. I don't even remember where --
exactly where it started, but I've been doing it since I was in
college. I used to make my roommates in college do it with me
and cut out pictures from magazines and glue them on
paper.

We'd go get the hot pink, big poster boards --

JASON HOWARD: Oh, goodness,
yeah.

SAVANNAH BARRY: -- and like glue stuff on
there. Yeah, I did that.

JASON HOWARD: It's almost like a high
school collage.

SAVANNAH BARRY: Yeah. But then when
I joined LinkedIn, we have these things called "in days" where we
have basically one day out of a month where we focus on doing
something outside of your job.

So every January, it's like a vision "in day." So they
actually encourage you to make mood boards. Like, okay,
perfect. (Laughter.)

So started doing it at work and now I work at home, so now I
have a little bit of a different vision board area, but yeah, it's
truly pictures, words, things that just inspire me and kind of keep
me motivated throughout the day, throughout the year, and just a
way to kind of keep myself accountable for the goals I set early on
in the year and just really make sure that those are staying top of
mind for me throughout the day.

JASON HOWARD: Was this something that you
did individually? Did your team come together and you kind of
like group -- encouraged each other? Like, what was that
process like?

SAVANNAH BARRY: Yeah, it was a little bit
individual, but I definitely tried to source feedback from, like,
my manager, my peers, like, here's kind of what I'm doing, do you
have any ideas on, like, professional goals that I should maybe
focus on for next year?

This year, one of my learning goals is SEO and SEM, which I
haven't really gotten my feet wet with yet, but my manager was
basically, like, "Hey, here's something that would be pretty
interesting I think for you to learn." And so that's another
thing that I'll be focusing on.

JASON HOWARD: I'm assuming SEO being
search engine optimization?

SAVANNAH BARRY: Yes. Yes.
Yes.

JASON HOWARD: Okay.

SAVANNAH BARRY: Thank you for
clarifying. (Laughter.)

JASON HOWARD: No, hey, I mean, you know,
this is my Microsoft, we use acronyms like they're going out of
style. (Laughter.)

So can you tell me a little bit about, like, your
decision-making process? You said in this circumstance, you
know, your manager, you know, you sought some feedback to help you
guide down that path, right? And, obviously, there's things
that you come up with on your own that you want to learn. So
how do you decide what's going to be the best use of your
time? Because, I mean, that's kind of the limiting or
deciding factor here is you have to make the time to do it, so
where does that decision process come from?

SAVANNAH BARRY: Yeah, you know, I really
try to focus on things that I think will help me become the
professional that I want to be, and really the person that I want
to be. I think about, "Where do I want to be in five years,
and like, what skills will help me get there?"

So I do a lot of research. I read a lot of blogs, I do a
lot of peer research, asking around, like, people who are in jobs
that maybe I aspire to be in, like, what are some skills that they
think helped shape their career, take them to the next
level?

And I usually start with a pretty long list. I'll, like,
throughout the year, I'll have, like, a running Word doc and I'll
just put stuff in there, and then I can reevaluate and say, "Okay,
here are the things that actually feel tactical for the
year." The UX one was definitely not on my list, it just like
-- my, like, obsession with, like, how I'm interacting with things,
I was, like, I need to. This is a learning thing that I need
to do, and I do think it'll make me a better marketer at the end of
the day. So that was an off-the-cuff add to the
list.

JASON HOWARD: Wait, so when you look at
the concept of lifelong learning, on the surface, it seems like
this great goal, everybody should be doing it, but given, you know,
we mentioned time a minute ago, some of the listeners are going to
sit back and say, "Hey, you know what? I'm crazy busy, I have
laundry to do, I've got work, I've got kids, I've got family, I've
got to feed the dog." Right? You know, I had to get up
at 6:00 in the morning, it feels like I don't get to sit down until
10:00, 11:00 at night. And it was never my time for me to
invest in myself.

So how do you stay motivated to make that time? How do you
drive yourself to make sure that you put it on the list of things
that you absolutely have to do?

SAVANNAH BARRY: Totally. I think
that everyone is very busy, and I think that's, like, in general, a
big blocker to learning for people. I've just found ways that
it organically works in my life.

So I listen to podcasts a lot. I'll find relevant podcasts
that are aligned to something that I'm currently learning.
And maybe that week I can only listen to a podcast while I'm
walking my dog. Like, that's all I can do. And that's
okay. Every action you take and every step that you take I
think is part of your learning journey, and not everyone has an
hour a week to carve out for learning, and that's okay.

If it's bi-weekly, if it's once a month doing two hours a day, I
think that, in general, if you need your support of your friends
and family and managers, like, it's fun to make it a little bit
more of a collaborative experience. Like, "Hey, guys, I want
to make time for learning, you guys should, too." And I think
that also helps create a little bit more accountability, and also
maybe frees up some time for you, if everyone around you knows that
it's a priority.

JASON HOWARD: So how has learning helped
you professionally?

SAVANNAH BARRY: Well, in general, I think
-- I've gotten a couple promotions within my role just specifically
because I've been able to go above and beyond of what my normal job
consists of. I think it -- in general, it's made me a great
cross-functional partner.

I mean, a lot of the work that I do in marketing, and I'm sure a
lot of other marketers out there, is very cross-functional.
You're working with a ton of different people, a ton of different
teams, and I think my desire to understand HTML, desire to
understand SQL, desire to, like, understand some of these things
that maybe I'm not using a ton, but other people are, has really
helped me to be a more empathetic partner, to be a more
constructive feedback-giver, it's just really helped me a lot in,
like, developing really strong relationships.

So I feel really lucky that I actually work on a learning
product, it's kind of crazy, it's truly the perfect job, I love
it.

But, yeah, I think it's just that curiosity and that desire to
always want to be doing more and really just -- that curious
mind. And I think it has helped me in my career, and it's
allowed me to start doing like more of a different marketing
role. And I was, like, "Ooh! This marketing role looks
interesting."

And so I started learning and developing and asking people who
did that job, like, "What does your day-to-day look like?"
And I was able to move into that role with not having the total
skillset that I needed to have, but I think my managers felt
confident that I knew what I was doing, and I could handle
it. And if I couldn't handle it, I would learn how to do
it. (Laughter.)

JASON HOWARD: So one important question
that I want other ask you is: How do you inspire somebody
else to learn? Through the conversation that we've had, it
seems a big piece of it is you have to have some of this natural
desire, right? If you're not the curious type, it sounds like
it could be much more difficult to kind of get personally
inspired. It's almost like you need to look externally for
some of that motivation.

You mentioned mentoring. That's one of the things that's
really important here at Microsoft is the concept of having a
mentor, finding somebody who's in a space, hopefully outside of
what you're doing, because at least within this company, there's a
lot of leaning on your team, leaning on your peers, like partner
teams, and you kind of naturally build up some of that learning
along the way as you work with other people, but having somebody
outside of the circle of which you normally focus on, they can give
you a much different perspective.

You know, obviously, this is a bit work focused, but they can
give you a much different perspective than the way that you are
accustomed to looking at things.

SAVANNAH BARRY: I 100 percent
agree. I think something that's been really valuable for me
is having those mentors who can help me look at what is outside of
my narrow range of focus. And as a mentor, that's something
that I strive to do, too, is say, "Hey, like, what do you want to
do? What do you want to learn? What do you want to be,
you know, five year -- two years, next month? What do you
want to be doing day to day?" And if that doesn't align with
what you're doing now, then how can we really set you up for
success to be where you want to be? What are those skills you
need to learn to get that promotion? What are those skills
you need to make a horizontal move?

And I think learning can be tied to your professional
goals. And I think so often we lose sight of what those goals
are. I mean, everyone is busy. Work is crazy, personal
lives are crazy, your kids are running all over the house.
Like, things are crazy. But I think if you keep in mind those
goals and talk to someone, find someone in a different organization
or different company, reach out to someone on LinkedIn and just
say, "Hey, I like what you're doing."

I find myself reaching out to a lot of people on LinkedIn to
just say, "Hey, I saw this blog post, would love to know how you
went from this job to this job. Do you have five
minutes?"

I just had coffee last night with a friend who reached out to me
because he wanted to learn more about what I'm doing
professionally. Like, he wants to make a career change.
And he's, like, "Hey, tell me about some of the skills you acquired
to be able to do that. Help me out.”

So I think just learning on other people and keeping true to
your goals and keeping true to who you are, that's really what
motivates me.

JASON HOWARD: Do you have any suggestions
on getting people started?

SAVANNAH BARRY: Yeah, I mean, it depends
on what you're trying to learn. I rely on our LinkedIn
Learning, like our own product a lot when I'm thing to learn more
of, like, the technical skills that I want for my professional
career.

An example, we have instructional designers on our team who
basically build out this learning path, and it basically takes you
through nine hours of learning, which is a lot, and not everyone
has that -- like, it's a collection of courses that it shows you
and tells you, "Hey, here's what to expect. Here's what
you're going to be learning." You can kind of see the courses
that you're going to be taking. And you can say, "Okay, this
is a very easy way for me to get started." I mean, that's
what I started doing for UX, I'm deciding to read this book in
parallel. That's what I'll be doing for SEO. We have a
learning path on LinkedIn learning that I'll be using. That's
what I did for HTML, it's what I did for SQL.

So I think there's people who have done a lot of the legwork for
you, and I think just finding a resource that aligns with what
you're trying to achieve.

So figure out that skill. What are some of the most
in-demand skills? What's going to take you to that next
level? And then find out where you can learn it.
Learning paths are a really, really great, easy way to absorb
information, and it's a lot of information. When I first
looked at it, I was like, "Okay, ten hours, wow.
Okay."

But when you actually think about it, that's the whole learning
journey right there, that's it all. Right there, in front of
your face, you can look at it on your phone, I listen to just the
audio sometimes if it's like more of a soft skill. There's
lots of ways to really engage with learning.

JASON HOWARD: Well, before we wrap up
here. Any final words of advice or life tidbits or any other
awesome vision board things you want to share with the
listeners?

SAVANNAH BARRY: Oh, gosh. Life
tidbits? I mean, I would just always stay curious, always ask
questions, and just keep learning, and have fun while doing it.
I just urge everyone to stay curious.

JASON HOWARD: Awesome. Thanks,
Savannah. Thank you so much for your time today.

SAVANNAH BARRY: Thank you.

JASON HOWARD: Appreciate you being
here. Hopefully, the listeners have enjoyed this as much as I
have.

SAVANNAH BARRY: Yes, me too. Thank
you.

JASON HOWARD: Cheers.

SAVANNAH BARRY: Bye.

JASON HOWARD: For tech professionals,
keeping up with the latest knowledge is everything. Have you
ever wanted to know if becoming a Microsoft Certified Solutions
Expert would be worthwhile? What about how to tackle the
amazing and sometimes overwhelming options to learn at Microsoft
Ignite?

We talk shop with our next guest, Aaron Buckley, a Windows
Insider and IT pro at the company Alex and Ani based in Rhode
Island. Good morning, Aaron, welcome to the Windows
Insider Podcast.

AARON BUCKLEY: Good morning.

JASON HOWARD: So, tell us about your
career as an IT pro.

AARON BUCKLEY: Yeah, sure. I got my
start in IT working at my college help desk. That evolved
into my actual career path. Even though I was not studying IT
in academia. And so now at my current company, Alex and Ani,
I kind of jokingly refer to myself as an "army of one,"
particularly with client management and devices.

I am running our Intune mobile device management, I am also
architecting and governing System Center Configuration Manager, and
I am in charge of leading the charge for Windows 10. We're
upgrading from a bunch of 7 and 8.1 machines.

JASON HOWARD: That is definitely an
interesting career path. I've got to tell you, you said that
you didn't go study IT in college. I'm actually in that same
boat, right? It's something that I haven't talked about on
any of the podcasts before, but I was fortunate enough to go to
university, and my degree is in economics. Right? And
here I am working at --

AARON BUCKLEY: Economics?

JASON HOWARD: Yeah. And here I am
working at Microsoft, right? Trust me, I did not see that one
coming.

AARON BUCKLEY: I might be able to beat
you in terms of relevance. My degree -- I got a double
bachelor's degree in psychology and in political science.
(Laughter.)

JASON HOWARD: All right.

AARON BUCKLEY: So I'm not sure how I got
to IT.

JASON HOWARD: You took a left turn at
Missoula, man.

AARON BUCKLEY: It's a passion.
(Laughter.) Yeah. I should say, you know, while I had
my interest in academia, I've always been an enthusiast for
technology. And so I actually consider myself really, really
lucky that as my career, I'm doing what I love. And I know
that that's kind of aspirational for a lot of people. I
somehow achieved this, I'm really proud.

JASON HOWARD: So I have had the pleasure
of speaking with you before. We actually met at Ignite last
year at the Windows Insider booth. We had several Insider
roundtables, met you there, learned a little bit about you there
and obviously, you know, happy to have you back and actually get to
talk to you on a more one-to-one type basis here.

Through some of that conversation, you know, found out that
you're a Microsoft Certified Solutions Expert. Side note for
our audience. You may be asking yourself, "What is a
Microsoft Certified Solutions Expert, or MCSE?"

These are folks who have achieved a Microsoft certification that
validates they have the skills needed in a particular area -- for
example, app development or cloud infrastructure.

Aaron, can you tell us why tackling the certification was
important for your career?

AARON BUCKLEY: That's a good question
because I've got to tell you, some of these exams, I think they
were actually tougher than writing some of my 25- or 30-page term
papers. (Laughter.)

For the first couple years of my post-college, entry-level
workforce, I was at the help desk level. And through just
demonstrating my technical competency, I got to be a level-three
help desk, or escalation technician.

But it was really at the point where -- I remember the
conversation. I went to my boss and I didn't throw it down,
but I handed him my certification saying that, "Wow, yeah, I really
am an MCSE." And it was actually a couple weeks after that
that I got my first post-help-desk promotion. And at that
point I joined my company's system engineering team.

And that stuck out to me because I wouldn't tell people that you
have to have a certification in order to jump to higher levels in
your technical career path, but it was a milestone and a marker
that I was able to hand my leadership, and they were able to say,
"Wow, you not only have you demonstrated to us that you know this
information, but you somehow convinced Microsoft that you know that
technology." (Laughter.)

And so that, I think, was really important. That was
fundamental. I'm going to admit that I definitely failed my
last MCSE exam three times before I finally nailed it on the fourth
attempt. And let me tell you, when I walked outside having
finally passed my certification, I screamed at the sky I was so
happy. (Laughter.) I mean it when I say that I think
these MCSEs gave me more of a challenge that some of my college
courses and final exams. You guys are not messing around.

JASON HOWARD: So, no doubt, you've
obviously gained a lot through this process personally, and of
course it's impacted you professionally. So kind of on a
broader scale, for others out there who may be considering
something like this, what is some of the extra value you see in
getting this type of certification? How would you apply it
more broadly?

AARON BUCKLEY: Jumping to college for a
second, a lot of times people emphasize at the point of going
through, like, structured college courses is to really build up
someone's critical thinking skills and the way that they approach
problems.

I would apply that same sort of ethos to the certification
process. I think that the way that I approach confounds now
in my system or broadly in IT is strengthened by some of the
problem-solving processes I picked up through the certification
process. Not just the particulars of my certification path,
like, "Oh, of course, that's where you go in the SCCM console for
that." But also just advancing my core understanding of basic
troubleshooting steps. Like there's an awareness of knowledge
that you get going through these certification processes that I
think really just levels up someone's engineering perspective, or
their troubleshooting perspective.

I'm trying to think of the right way to describe this.
It's almost like a refining of the way that I approach
problem-solving. Does that make sense?

JASON HOWARD: Yeah, absolutely. If
I'm interpreting some of what you said correctly, it's -- part of
it is learning the actual materials that you're reading through,
right? Some of it's going to be new stuff, you'll pick it up
along the way, you'll get a chance to, you know, take a preview
build and go tinker around and see how it works and see how it
functions. But on top of actually covering just the specific
materials, it's changing the way you think about what you do
already and you've found some ways to kind of tweak and enhance and
gives you new products in just some of your day-to-day type
activities.

AARON BUCKLEY: Absolutely. And I
think that's something that Microsoft in the certification process
does really well, and I think it's part of Microsoft's
intent. As you're going through these certifications, they're
updated constantly, like, I think yearly. Like, the questions
you're asked, the technologies you're asked about. And I can
definitely say that the actual certification and testing process
has made available to me the various ways that I can solve
particular problems.

Like, for example, there have been a couple of times where,
after going through my Windows 8 MCSA, I realized that there were
so many things I was doing wrong, or just not doing the best way
with even just customizing a Windows image.

And then I take some of that that I've learned and I'm, you
know, using PowerShell to strip out -- sorry Microsoft -- the
default Modern applications that are in your corporate image.
Maybe my users don't need Candy Crush pre-installed.

But even then, like, a recent example would be a problem that I
have at my company is that we have a bunch of iOS devices that I
have governed through SCCM and Intune, sort of your hybrid
solution. And we've run into some issues because iOS devices,
we have no way to govern updates for them, and that's important
because my company has a number of line-of-business apps that are
made for certain versions of IOS.

Testing might not be fully complete for updating that app to the
next version of iOS. Well, I mean, it turns out that I
learned in some of my recent certifications that testing that
Intune standalone, Intune based in the Azure portal does have these
iOS update policies. So now that has directly informed me for
the next six months or so that I have some architectural changes
I'm going to be making to my device management and governance
structure.

And that's something that I probably wouldn't have known right
off the bat unless it was being made available to me through this
process. Just one example.

JASON HOWARD: That's awesome.

AARON BUCKLEY: Really helpful,
actually. (Laughter.)

JASON HOWARD: So I'm going to shift gears
on you a little bit here. On top of just certifications and
things of that nature, obviously Microsoft has many events
throughout the year. Right? We have Build, we have
Ignite. I mentioned at the beginning of the show, you know, I
actually had met you I person last year at Ignite. What do
you think about these types of events? For somebody who
hasn't been to Ignite before, say they're presented with the
opportunity this year, right? Do you have any, like, extra
tips for them to try to get the most out of the
experience?

AARON BUCKLEY: I have been privileged
enough, and really it is a privilege to have been able to attend
two Microsoft Ignite conferences. Certainly, I'm really
hoping my company would send me for a third time this year.
And that is because of how much I've learned.

Ignite isn't a vacation, it's definitely a working trip.
And my first trip to Ignite, I would look around and see everyone,
you know, sitting on couches on their computers. And I'm,
like, "What are you guys doing? There are so many trainings
to do, and there's this event!" (Laughter.) No, no, no,
they had the right idea, I understand why they are taking things
they're learning from these hands-on opportunities and starting
right away in their environments.

I would recommend that people go through the actual schedule,
it's up a month or so before the actual conference. Go
through, pick out a good five or six knowledge areas that you are
executing against in your company. Pick those areas and go
through and add them all to your scheduler. I understand that
at the end of that process, you are going to probably be triple or
quadruple booked at probably every time slot available, but what
I've found is that instead of trying to really structure my
itinerary to Ignite, layer it all on and pretend you're Hermione
Granger with the Time Turner and that you're going to attend them
all because I've found that, you know, Microsoft does all of us a
really great service by recording all these workshops.

You're going to be able to attend one per time slot, you know,
in person. Go to the one that you think that if you had the
opportunity, you would like to talk to the people hosting those
particular workshops. The other ones, if they're just
technical deep dives or maybe introducing new technology, keep it
on your schedule, but definitely be sure to go back on your own
time after the crunch of the conference week is over, look through
all those videos and actually catch up. Thank you, Microsoft, for
providing this as a service.

If you can't attend Ignite, I find that a lot of those videos
also find their way to the Microsoft Mechanics site, also Microsoft
Virtual Academy. And so all of that is available to
you.

I would also recommend that even if you've layered up your
schedule, it can feel intimidating. Your phone's buzzing a
lot with alerts for all these workshops and such. Be sure to
actually allow yourself some down time, because it's not going to
be helpful to you to be sitting through five straight hours of
workshops and then you sit down at the end of the day, and you're
trying to remember this massive information dump that you sat
through. No, it's okay to actually skip a session here or
there, some are on repeat later on in the week.

I mean, it probably sounds a little cliché, but take care of
yourself. Give yourself time to sit down at lunch, absorb the
morning, and prepare yourself for the next round of workshops later
on in the day. That's something that I did not do my first year,
and I came back thinking that I somehow needed to, in a panic,
restructure all of the systems in my company. There was this
crazy anxiety that came from feeling so -- again, I said this word
like three times, but so "empowered" by the experience at Ignite.
That's some quick survival advice I'd give.

So kind of on a personal level for a moment, for you as an
individual, what drives you to keep learning?

AARON BUCKLEY: I'm constantly refining my
processes. And as I gained more information, primarily from
Ignite and these training videos, I am all the time sort of
revising, refining, solving for efficiency, solving for capability
-- all these things. And I've found maybe a little too much
of a technologist at this point, but I found that that perspective
has been informing me in the broader and broader aspects of my life
including, you know, going to the gym and working out and a more
healthy lifestyle. Even my personal finances and such. I've
almost found that I'm taking this systems perspective and applying
it to so many components of my life. I can't really help laugh at
it sometimes, you know? In a good way.

JASON HOWARD: Almost like the challenge
of it is, in and of itself, a solid reward that keeps motivating
you.

AARON BUCKLEY: Oh, without
question. I guess when I was growing up, I always had this
fear of being stuck in a redundant, boring -- I've got to invoke,
like, Office Space here, that sort of job situation.
And so working in IT where -- I mean, depending on where you work,
every day is a whole, bright, new crisis to solve. That's
something I get a lot of personal and professional fulfillment out
of.

JASON HOWARD: Yeah, I have to say,
obviously being a different person, I take some of that same
challenge, and that's part of what keeps me interested in my job is
each day that I log into Twitter and I talk to some Insiders, see
what they have to say, did they like the newest build? What
kind of crazy stuff did somebody find? And unless it's a
broad, widespread issue, every day that I log in, I either learn
something new, I meet somebody new.

AARON BUCKLEY: Definitely.

JASON HOWARD: I have the chance to learn
something about Microsoft technology that I never knew because it's
not something I had ever touched before.

I'm going to be writing a blog post here pretty soon on the
topic of legacy filter drivers, and you know, some bugs that we
worked through. And it was before this bug came up, I
honestly had never heard of it. I had interacted with them
before, right, as an end user, but it was one of those things that
it was just part of the operating system, part of the software I
was using, and at the same time, you don't know what you don't
know. Until I was faced with the need to learn it, I didn't know it
was something that I needed to go and learn about. And now
that I know more about it, it's fascinating.

And I'm, like, "Oh, my goodness, there is a lot surrounding
this." And it's amazing how -- without getting too deep into
the technology side of it -- one little change can have some really
big outcomes, whether those changes are expected, and sometimes
unexpected. But the learning aspect of it is one of the key
factors for me that keeps me really excited about my job because
every time I get asked a question about something that I don't know
about, it means that I have to go learn something.

AARON BUCKLEY: So, cars. I come
from a working-class family. I have a couple uncles, a
cousin, a grandfather who are all car mechanics. And so I'm a
computer engineer, I eventually got so aggravated -- not on my
current car, I love my car -- but an older car. The "check
engine" light was constantly always on. And that is horrible
for a computer technician. It's, like, "Oh, my God, there's
an error message. There's an error code. I must
fix."

Instead of putting black electrical tape or something over the
"check engine" light, I sort of started the conversations with my
family of, "Okay, I need to replace this thing, Uncle. I
don't want you to do it, this is my car, I'm used to fixing
machines, I am informed by my passion for computers and fixing
those machines."

So it's really funny. I then -- sort of applying that same
ethos to learning how to fix my own car. I can replace my
tire, I even replaced my own brakes a couple weeks ago. Kind
of proud of that.

JASON HOWARD: Well, Aaron, it has been a
pleasure chatting with you.

AARON BUCKLEY: Thank you so much for
having me.

JASON HOWARD: Take care. Cheers,
man.

AARON BUCKLEY: Cheers.

JASON HOWARD: By now, we hope you're
inspired to grab lifelong learning by the horns and maybe even make
a vision board or tackle a Microsoft certification.

Our final guests are going to share a few more tips, and some
exclusive resources available to Windows Insiders. Here's
Thomas Trombley, senior program manager here at
Microsoft.

THOMAS TROMBLEY: You may have heard that
Microsoft purchased LinkedIn, which purchased Lynda.com a few years
ago.

Now, LinkedIn Learning combines all the great content of
Lynda.com -- that's more than 10,000 courses spanning business to
tech skills and creative skills, with the personalization powered
by LinkedIn.

Here's a pro tip: Windows Insiders get access to free
LinkedIn Learning courses, and we'll let you know how to access
those at the end of this podcast. We'll also have a surprise
giveaway. Stay tuned for how to enter.

JASON HOWARD: Thomas is here with our
second guest, Doug Winnie.

DOUG WINNIE: My name is Doug Winnie, I'm
the chief evangelist and head of community for LinkedIn
Learning.

THOMAS TROMBLEY: Some of our listeners
may not know that LinkedIn is now in the Microsoft family.

DOUG WINNIE: Uh-huh.
(Affirmative.)

THOMAS TROMBLEY: What do you find most
exciting about LinkedIn now being part of Microsoft?

DOUG WINNIE: It's interesting because the
culture of the whole LinkedIn experience is still very much
LinkedIn.

THOMAS TROMBLEY: Right.

DOUG WINNIE: But now we have the benefit
of everything we have from Microsoft. So I go to work, I go
to a LinkedIn building, I'm able to exchange and do everything,
just what we always did, so I don't feel that anything has changed,
and everything's been going wonderfully.

THOMAS TROMBLEY: Now, what is LinkedIn
Learning versus the LinkedIn social network and platform that most
people are familiar with? And how do the two sort of play off
one another?

DOUG WINNIE: So your LinkedIn profile is
essentially the front door for all your skills, your background,
your experience, volunteer opportunities. But LinkedIn
Learning is able to tie in the skills that you currently have, job
opportunities that you're looking to get, and can connect all the
learning content that we have to the skills that you want to
achieve a change in your career or to apply for another
position.

THOMAS TROMBLEY: Right.

DOUG WINNIE: Or to look at areas that you
want to improve, to maybe do a career shift, or to maybe do a side
hustle.

THOMAS TROMBLEY: We're going to talk more
on side hustling in a moment.

DOUG WINNIE: Awesome, okay.

THOMAS TROMBLEY: Online learning isn't
just for students anymore, but people of all stages in their
careers. It just seems to have exploded in popularity.
Can you talk about some of the trends that you're seeing in
technology and in the job market that are driving this wave of
lifelong learning, especially through platforms like LinkedIn
Learning?

DOUG WINNIE: We have this model that we
talk about inside of LinkedIn called The Four Squares. The
Four Squares involve major steps that you're taking over your
evolution in your position.

You first start off as, like, the eager beaver. I'm ready,
this is my first job, I'm really excited, and I'm going to nail it,
okay?

And then you get to this point where it's like -- not quite
sure, maybe I bit off more than I can chew. But then you
start doing one thing. You do one task, you get a little bit
of confidence going into that. And you're, like, "I got this,
I can do this."

Then you start doing meatier and larger projects, and you get to
the mastery part. Each one of these four squares represents a
step on the journey that you're taking in your career. Could
be a career, could be a job, but it could also be something you're
doing outside of your job like a side hustle or some sort of
volunteer activity.

THOMAS TROMBLEY: Right.

DOUG WINNIE: What's important, though, is
as you're navigating from square to square, you need to find a new
way to engage with your learning because you might have technical
skills that you need to get from, say, eager beaver to, "Oh, my
God, I'm not going to be able to do this." To focusing not
just on what you're doing, but how you're doing it. To talk
more about the interpersonal. You might have some life
situations that are coming into the workplace, things like that
that are not the technical tactical things, but they help you kind
of get through roadblocks or hurdles that you need to overcome in
order to get your job done.

What happens, though, is when you look at all these four
squares, people think that they are in one of these squares at one
time. In reality, you actually are in all four at the same
time. Whether I'm in my career, I'm in my job, whether I'm a
parent or a new parent, you know? My baby's born, this is
awesome! And then you're, like, "I'm responsible for a
child." You know, this is hard.

All these different things exist at the same time. So if
you look at it from that perspective, there's this constant cycle
of needing to learn as you're going through this process.

THOMAS TROMBLEY: Kind of somewhat of a
segue to this four-square approach, or this thought process, it
kind of feels like a pendulum going back and forth.

But I recently read a book by Angela Duckworth called
Grit, I don't know if you've ever read it. She
shares stories about people striving to succeed, building
perseverance and resilience into what she calls, well,
"grit." Doug, do you find it difficult or tough for folks to
stick to classes on LinkedIn Learning, given how busy life can
be? Like, how do people have the grit to really see their
learning through?

DOUG WINNIE: Everyone has a different
approach to what they need to learn. So sometimes we'll have
people that want to tackle a really long learning path, which is a
sequence of courses that we've created that might map to a
certification, like the Associate Android Developer Certification,
which we recently partnered with Google on.

Then we also have PMP certifications and other things that, you
know, are very long-tail approaches. But sometimes you need
to just have that one thing that you need to get you through what
you're troubled with today.

And it's funny you talked about the grit. We just launched
a course with Sheryl Sandberg and Adam Grant on Option
B.

THOMAS TROMBLEY: Oh, yeah.

DOUG WINNIE: Around resilience at
work. We just launched that this month. And the nuggets
that are inside of that, that if you just can watch one thing just
to help you through a setback or a hurdle that you're having and to
renew the positivity that's inside of you that you know is there,
that's just being kind of --

THOMAS TROMBLEY: Right.
Right. Exactly.

DOUG WINNIE: -- pushed down, that can
then propel you forward and then be able to go back onto your
journey.

THOMAS TROMBLEY: And I think that offers
some of the value proposition around online learning. Like,
there's this explosion of online learning opportunities that can
kind of give you that "oomph" you need. And I wonder if you
could talk a little bit about how LinkedIn Learning's offerings
different from, say, your competitors at, like, Treehouse, you've
got Code Academy, there's Udemy, and the like.

DOUG WINNIE: I'd say the
flexibility. So just like I mentioned, if you want to go
through a long path, you can do that. If you want to just
take one course to get you through a skill that you're trying to
work on, or just that one video.

The mobile applications that we have integration with LinkedIn,
I mean, all of these things combined make it flexible for what you
want to get out of it.

A lot of times when I talk to someone that's really struggling
with, "What do I need to know? What do I need to
learn?" Sometimes, they focus on the skills, they focus on
the technology. "I need to do this, so I, therefore, need to
know C#, I need to do all these programming languages and tactical
things."

THOMAS TROMBLEY: Right.

DOUG WINNIE: And I say, "Lead with your
feelings. What do you want the emotional outcomes to be of
what you're doing?" And look at that as another way to
approach your learning.

Because the skills we have on LinkedIn and how you can build
your profile is able to accommodate those more emotional social
aspects of how you do your work, that creates a really unique way
of building your learning journey on LinkedIn Learning as opposed
to our competitors.

THOMAS TROMBLEY: That's really
compelling. I feel like you need to teach a course on just
preparing to learn or an equivalent.

THOMAS TROMBLEY: I think a lot of
professionals these days can identify with having a side hustle, as
you mentioned earlier, or wanting to make a big shift in their
careers. Could you share with us a story about a LinkedIn
learning participant you know or heard about that successfully fed
their side hustle?

DOUG WINNIE: There's one person,
Sebastian Bleak, I read about his story recently. And he
recently had basically lost everything. Lost his job, lost
his home, everything, was basically living out of his
car.

And what turned into a career for him started off as just
something very small, a little nugget.

A friend of him said, "Just learn one thing, one thing every
day. It doesn't matter how small, doesn't matter how
insignificant you think that it might be. Just one
thing."

So in his car, he was basically going through the library
learning things like around illustration, graphic design, and
through just chipping away at it one day at a time, he was able to
get a job at an awesome graphic design company in LA, and he's now
an instructor with us, actually, covering T-shirt design.

THOMAS TROMBLEY: That's
amazing.

DOUG WINNIE: But the thing is, if you
think about it as just one little chip that you can do to this
giant statue that you're trying to create, okay? It can be
overwhelming when you think about the vast amount of things you
have to learn. But if you just do it from a very agile
approach and thinking about it as just, "What am I doing today to
get there?"

THOMAS TROMBLEY: I feel like all too
often we get so focused in our day to day -- like, I personally
have a to-do list that's a mile long and I sat there and mapped it
out in Excel and it said one day to complete all those tasks would
take 25 hours per day. (Laughter.)

DOUG WINNIE: I have, you know, we talked
about this before the show. I've got some tattoos. And
I have one on my arm. My husband, he always tells me, "Stop
planning. Stop planning everything. You always are
planning everything, why aren't you actually doing the things that
you plan?"

So I actually have that on my arm as a constant reminder to say
it's not just about planning and creating to-do lists, it's about
checking them off and having that sense of accomplishment at the
end. That's part of education, part of learning as
well. Don't get overwhelmed by the sheer vastness of what you
have to learn. What did I learn today? And take pride
in the fact that you learned that.

THOMAS TROMBLEY: Yeah, I remember my mom
would always say life is what happens when you're busy making other
plans.

DOUG WINNIE: So, we've got some
opportunities for the Windows Insiders to take courses on LinkedIn
Learning. And Insiders can stay tuned for the next Windows
Insider newsletter to arrive in their e-mail. And that will
include codes to select free courses.

And what we've done is every single month, we have courses from
business, technology, and creative libraries, and we recently
launched it so that people that are getting the German, French,
Spanish, and Japanese editions of the newsletter get localized
videos for those languages.

The other thing is tying in with why we're all here in Redmond
this week. We have about 16 courses for our Microsoft MVPs
that cover technology from all kinds of different topics --
business, creative, and technology -- and we're unlocking those
courses along with the traditional four that we do every single
month.

So, that's great to see how we're taking the strength of the
Microsoft leadership community and our community leaders and
showing how they are able to give and provide their expertise on
LinkedIn Learning.

THOMAS TROMBLEY: Right.

DOUG WINNIE: So there also is going to be
a Twitter contest that we're running. And for --

THOMAS TROMBLEY: Ooh!

DOUG WINNIE: Ooh! For those that
are listening, we're doing a three-month subscription giveaway for
LinkedIn Learning. So if you win this, then you'll get access
to LinkedIn Learning plus other LinkedIn career premium benefits to
help you with your job hunt, you're looking at salary information
or other aspects to basically boost your game on
LinkedIn.

THOMAS TROMBLEY: Right.

DOUG WINNIE: So what we ask you to do is
tweet all the new talents and knowledge that you've gained through
LinkedIn Learning and we'll randomly select someone to
win.

So to enter, you need to let us know on Twitter how you've used
LinkedIn Learning, then tag your tweet with #AlwaysBeLearning and
#WindowsInsider, and then we'll enter you into the
drawing.

And if you want more information about the contest instructions
and rules, you can see that on the Windows Insider
website.

THOMAS TROMBLEY: Let's talk a little bit
more about how these folks could get started. Do you have any
tips for folks who want to get started with LinkedIn Learning,
like, for anyone who might be feeling excited, but may be
overwhelmed by having so much knowledge at their fingertips?
It can be a little daunting when you see the catalogue.

DOUG WINNIE: It is. One of the
things that's unique is when you go to LinkedIn for the first time,
you can identify key skills that you're looking to learn.
Based on that, it will then create and curate a selection of
courses based on those.

You can then go in and modify. You can add one, you can
remove one. That will continue to kind of shape the
recommended courses that are there.

The other idea is to look for a career or look for a job that
you are looking to achieve and if you can do that, you can see on
LinkedIn all the skills that are required to get that, and you can
compare yourself to see, like, all right, how do I match up to that
particular job?

Then take those skills and feed them into LinkedIn Learning so
you can build a list of courses there.

The last one is to go through our learning paths. They
look daunting at first, but if you look at them from one step at a
time, just like I said, one day learning one thing, you will get
through and build the statue by chipping away at it one day at a
time.

There all kinds of learning paths based on business, creative,
and technology careers and topics that are then segmented down into
specific job roles or if you're a new manager or if you're entering
into an executive or leadership position, there are all kinds of
courses that we curate in learning paths to help you down that
path.

THOMAS TROMBLEY: Let's talk about your
own learning path. We've talked about learn one thing every
day, your arm says, "Stop planning." You know, what are you
learning these days? Any secret things you're -- or hobbies
or learnings that you're working on right now?

DOUG WINNIE: So when we talk about side
hustles, for me, it's not necessarily a side hustle, it's just
something that I love to do. I love teaching. And I've
got my job at LinkedIn, which I love, but I really enjoy being in
front of people and teaching and giving back all the skills that I
have amassed in my career.

So I've got 20 courses on LinkedIn around learning how to code
and product management, I was a product manager for many, many
years prior to coming to LinkedIn.

But I wanted to make that different for me, so I became a
teacher. So I'm a part-time AP computer science teacher at a
local high school in the Bay Area.

The experience and the energy I get from that, but also the
different challenges of looking at how do I approach a classroom is
a learning opportunity for me. And what's been fascinating is
taking my product management skills where I look at things as
agile, I put together roadmaps and I am constantly doing feedback
from people on an engineering team or a design team and bringing
that to the classroom. Using a lot of the things that are on
LinkedIn to help me with gathering data, to put together data
visualization and to create a compelling story as to how the
students in my class have ownership of the classroom and how I
teach has been wonderful. It's been fascinating because they
feel, and they do, have ownership of how I teach. What do I
change? Do I do more of this? Do I do less of
this? Do I ditch my lecture notes and do slides
instead? And they're able to add and have ownership as to how
they want to learn.

THOMAS TROMBLEY: It sounds more
collaborative. Like, they have a stake in the game in some
way and in that, there's a vested interest.

DOUG WINNIE: And they know that I'm
accountable to them. When you think about a lot of teachers
and a lot of classrooms sometimes that's not necessarily the case
-- at least it was when I was a kid, where it was, you know, "I'm
gonna teach this way, this is how it's going to happen."

But when you take skills from other careers or other tracks and
are able to kind of blend them together, that's where you're able
to unlock about how you can change the way that you approach your
career, and hopefully be a ripple effect to other people.

THOMAS TROMBLEY: That's inspiring.
I happen to know that you're a teacher.

DOUG WINNIE: Okay.

THOMAS TROMBLEY: I didn't know you were
teaching high school kids part time. I don't know how you can
do that.

DOUG WINNIE: I'm also a part-time varsity
lacrosse coach as well, so --

THOMAS TROMBLEY: Okay, now I'm feeling
lazy.

DOUG WINNIE: No, no, no.

THOMAS TROMBLEY: All right, well, I
discovered yesterday that you have a huge presence. You're
almost somewhat of an Internet teacher celebrity of sorts as a
programming and technology-focused teacher.

DOUG WINNIE: Okay.

THOMAS TROMBLEY: I saw you have a
Computer Science Principles lab on C# with 100,000
views. You have the Android App Development Quick
Start, which I think you mentioned earlier, and that's got
300,000 views. Programming Basics, half a million
people -- Programming Basics, half a million views.
I even saw one on Windows Phone 8 development.
(Laughter.) Which actually brought me over to Microsoft a
little over five years ago.

As a PM, I'm also looking forward to taking your Product
Management Foundations course, it's been added to my
list. But what really got you interested in teaching
technology?

DOUG WINNIE: When I was a product manager
at Adobe, which if you go to my LinkedIn profile, you'll see very
clearly listed there. I managed a lot of the developer
interactive products that we had.

And I'm the kind of product manager that approaches everything
with compassion for the user, understanding the problems that
they're having, and good compassion for the struggles that they are
experiencing with their products.

I can approach that by improving the products, but I can also
approach that by helping people learn how to use the products and
the technologies that are there.

So when I was a PM on the side, I did a series on programming
and scripting with Adobe products. And it was just something
I liked to do, I wanted to help. I wanted to share what I
knew with other people.

So I did that, and it was a big success. And it led to a
couple books, it led to some other teaching opportunities at places
like San Francisco State and other places. But I found that
doing that gave me a new perspective in terms of how I could help
people in a virtual way, because I always saw it as kind of a
classroom thing where I had to be physically with them.

Because of the power of the Internet and video and being able to
connect with all these different people, gave me an audience that I
never thought that I had.

When I left Adobe and went to Lynda, I've now had even more
people that I was able to really talk to. And with LinkedIn,
we have over half a billion members on LinkedIn.

THOMAS TROMBLEY: Monstrous.

DOUG WINNIE: When we think about the
power that everyone individually has to write articles, to write
short-form posts, or even with your phone, just record a video
right with the LinkedIn app on your phone and just immediately put
it up there to talk about something that you're going through today
or a quick tip about how you were able to solve a problem
yourself.

THOMAS TROMBLEY: Right.

DOUG WINNIE: You can immediately learn
and teach at the same time on LinkedIn. That got me really
excited.

So I joined the content management team, trying to find awesome
people to help add more of their experience onto the platform, and
then eventually I wanted to connect all these communities together,
which led me to my job today.

THOMAS TROMBLEY: That's a tremendous
amount of value under that big umbrella that you
described.

DOUG WINNIE: It's overwhelming
sometimes. But on the same note, I feel lucky to be able to
have this opportunity.

THOMAS TROMBLEY: Doug Winnie, it's been
really inspiring to speak with you today. There's a sign that
sits outside my office that says, "The only place that learning
comes before knowing is in the dictionary." And I feel like
newly inspired to jump back on my own educational program.
And I hope some of our listeners do as well. Thank you for
your time today.

DOUG WINNIE: Thank you. It's been
wonderful being here and I'm thankful that I can be the drop to
create the ripple effect.

JASON HOWARD: Thanks for listening to
this episode of the Windows Insider Podcast. Get the
podcast automatically every month by subscribing on your favorite
podcast app. Until next time, Insiders.

NARRATION: The Windows Insider
Podcast is produced by Microsoft Production Studios and the
Windows Insider team, which includes Tyler Ahn -- that's me --
Michelle Paison, and Ande Harwood, and Kristie Wang.

Visit us on the Web at insider.windows.com. Follow
@windowsinsider on Instagram and Twitter.

Support for the Windows Insider Podcast comes from
Microsoft, empowering every person and every org on the planet to
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Please subscribe, rate, and review this podcast wherever you get
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Moral support and inspiration come from Ninja Cat, reminding us
to have fun and pursue our passions. Thanks, as always, to
our program's co-founders, Dona Sarkar and Jeremiah Marble.

Join us next month for another fascinating discussion from the
perspectives of Windows Insiders.

About the Podcast

The Windows Insider Team is taking the podcast airwaves to share all things future of Windows, Insider community and beyond.